This chapter provides a longitudinal analysis of Italy’s national digitalization strategy, examining efforts from the early 1990s to 2024. The chapter highlights how institutional fragmentation and political turbulence were progressively overcome by a strategic policy shift in 2016, when a dedicated Digital Service Team led by Commissioner Diego Piacentini initiated a transformative reform agenda. The Team focused on data interoperability, digital citizenship, and dismantling information silos. Key change mechanisms identified include reshaping public sector narratives, leveraging external expertise, building coalitions, and introducing agile coordination tools. These efforts led to the partial but significant institutionalization of digital platforms like SPID, ANPR, pagoPA, and App IO. Despite structural challenges, the policy achieved continuity across administrations and increasingly rooted change through a corporate governance model (PagoPA S.p.A.). The chapter shows how institutionalization, rather than radical disruption, became the engine of durable transformation—pointing to the importance of pragmatic, politically aware strategies in achieving digital governance objectives.